6-O-foliamenthoylmacfadienoside - Compound Card

6-O-foliamenthoylmacfadienoside

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6-O-foliamenthoylmacfadienoside

Structure
Zoomed Structure
  • Family: Plantae - Plantaginaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles OC/C=C(\CC/C=C(/C(=O)O[C@@H]1C2O[C@@]2(C2[C@@]1(O)C=COC2O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O)CO)\C)/C
InChI InChI=1S/C25H36O13/c1-12(6-8-26)4-3-5-13(2)21(32)36-19-20-25(11-28,38-20)18-23(34-9-7-24(18,19)33)37-22-17(31)16(30)15(29)14(10-27)35-22/h5-7,9,14-20,22-23,26-31,33H,3-4,8,10-11H2,1-2H3/b12-6-,13-5+/t14?,15-,16?,17+,18?,19-,20?,22+,23?,24+,25-/m1/s1
InChIKey JFJFTABVFYQANM-UGDFTMDRSA-N
Formula C25H36O13
HBA 13
HBD 7
MW 544.55
Rotatable Bonds 10
TPSA 208.13
LogP -2.26
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 544.22
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Anarrhinum pedatum Plantaginaceae Plantae 2500742

Showing of synonyms

  • Beladjila K.A, Berrehal D, et al. (2019). Antiangiogenic Activity of Compounds Isolated from Anarrhinum pedatum. Journal of natural products, 2019, 82(3), 510-519. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 544.55 g/mol

Structure

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 544.55 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 544.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.71
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.03
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
30.29
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.95
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.72
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.78
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1616.96
Rat (Acute)
2.81
Rat (Chronic Oral)
3.61
Fathead Minnow
4.06
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
501.9
Hydration Free Energy
-3.1
Log(D) at pH=7.4
-1.17
Log(P)
-0.95
Log S
-1.7
Log(Vapor Pressure)
-12.66
Melting Point
110.94
pKa Acid
5.25
pKa Basic
3.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8610
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8301
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7806
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7475
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7269
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7211
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7169
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7162
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7152
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7151
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7112
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7052
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7012

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